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Details

Stereochemistry ABSOLUTE
Molecular Formula C23H29N5O8S2
Molecular Weight 567.635
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of CEFCAPENE PIVOXIL

SMILES

CC\C=C(/C(=O)N[C@H]1[C@H]2SCC(COC(N)=O)=C(N2C1=O)C(=O)OCOC(=O)C(C)(C)C)C3=CSC(N)=N3

InChI

InChIKey=WVPAABNYMHNFJG-QDVBXLKVSA-N
InChI=1S/C23H29N5O8S2/c1-5-6-12(13-9-38-21(24)26-13)16(29)27-14-17(30)28-15(11(7-34-22(25)33)8-37-18(14)28)19(31)35-10-36-20(32)23(2,3)4/h6,9,14,18H,5,7-8,10H2,1-4H3,(H2,24,26)(H2,25,33)(H,27,29)/b12-6-/t14-,18-/m1/s1

HIDE SMILES / InChI
Molecular Formula C23H29N5O8S2
Molecular Weight 567.635
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 1
Optical Activity UNSPECIFIED

Description
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/18347113 | https://www.ncbi.nlm.nih.gov/pubmed/26440444

Cefcapene is a semisynthetic third-generation cephalosporin with antibacterial activity. Cefcapene binds to and inactivates penicillin-binding proteins (PBPs) located on the inner membrane of the bacterial cell wall. PBPs are enzymes involved in the terminal stages of assembling the bacterial cell wall and in reshaping the cell wall during growth and division. Inactivation of PBPs interferes with the cross-linkage of peptidoglycan chains necessary for bacterial cell wall strength and rigidity. This results in the weakening of the bacterial cell wall and causes cell lysis.

Originator

Approval Year

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Penicillin-binding protein 1A
45
Target ID: P02918
Gene ID: 947907.0
Gene Symbol: mrcA
Target Organism: Escherichia coli (strain K12)
Inhibitor
8504
Inhibitor
8504
Inhibitor
8504
 2.0 nM [Ki]
Inhibitor
8504
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Approved
8583
Giasion

Approved Use

GIASION is indicated for treatment of the following infections caused by susceptible microorganisms: (see section 5.1 pharmacodynamic properties): Pharyngo-acute tonsillitis Acute maxillary sinusitis Acute exacerbation of chronic bronchitis Community acquired pneumonia, mild or moderate Infections uncomplicated skin and skin structures, such as cellulitis, wound infections, abscesses, folliculitis, impetigo and boils.
Primary
Not Provided
511
Unknown

Approved Use

Unknown
Doses

Doses

DosePopulationAdverse events​
200 mg 3 times / day multiple, oral
Highest studied dose
Dose: 200 mg, 3 times / day
Route: oral
Route: multiple
Dose: 200 mg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/1503438/
healthy, ADULT
Health Status: healthy
Age Group: ADULT
Sex: M
Food Status: FED
Sources:
https://pubmed.ncbi.nlm.nih.gov/1503438/
Sources:
https://pubmed.ncbi.nlm.nih.gov/1503438/
450 mg 3 times / day multiple, oral
Highest studied dose
Dose: 450 mg, 3 times / day
Route: oral
Route: multiple
Dose: 450 mg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/15587753/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: FED
Sources:
https://pubmed.ncbi.nlm.nih.gov/15587753/
Other AEs: Eosinophilia, Epigastric pain...
Other AEs:
Eosinophilia (grade 1-2, 5%)
Epigastric pain (grade 1-2, 1%)
Eosinophils increased (grade 1-2, 2%)
Elevated transaminases (grade 1-2, 1%)
Blood urea nitrogen increased (grade 1-2, 1%)
Alkaline phosphatase increased (grade 1-2, 1%)
Amylase increased (grade 1-2, 1%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/15587753/
AEs

AEs

AESignificanceDosePopulation
Alkaline phosphatase increased grade 1-2, 1%
450 mg 3 times / day multiple, oral
Highest studied dose
Dose: 450 mg, 3 times / day
Route: oral
Route: multiple
Dose: 450 mg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/15587753/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: FED
Sources:
https://pubmed.ncbi.nlm.nih.gov/15587753/
Amylase increased grade 1-2, 1%
450 mg 3 times / day multiple, oral
Highest studied dose
Dose: 450 mg, 3 times / day
Route: oral
Route: multiple
Dose: 450 mg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/15587753/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: FED
Sources:
https://pubmed.ncbi.nlm.nih.gov/15587753/
Blood urea nitrogen increased grade 1-2, 1%
450 mg 3 times / day multiple, oral
Highest studied dose
Dose: 450 mg, 3 times / day
Route: oral
Route: multiple
Dose: 450 mg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/15587753/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: FED
Sources:
https://pubmed.ncbi.nlm.nih.gov/15587753/
Elevated transaminases grade 1-2, 1%
450 mg 3 times / day multiple, oral
Highest studied dose
Dose: 450 mg, 3 times / day
Route: oral
Route: multiple
Dose: 450 mg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/15587753/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: FED
Sources:
https://pubmed.ncbi.nlm.nih.gov/15587753/
Epigastric pain grade 1-2, 1%
450 mg 3 times / day multiple, oral
Highest studied dose
Dose: 450 mg, 3 times / day
Route: oral
Route: multiple
Dose: 450 mg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/15587753/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: FED
Sources:
https://pubmed.ncbi.nlm.nih.gov/15587753/
Eosinophils increased grade 1-2, 2%
450 mg 3 times / day multiple, oral
Highest studied dose
Dose: 450 mg, 3 times / day
Route: oral
Route: multiple
Dose: 450 mg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/15587753/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: FED
Sources:
https://pubmed.ncbi.nlm.nih.gov/15587753/
Eosinophilia grade 1-2, 5%
450 mg 3 times / day multiple, oral
Highest studied dose
Dose: 450 mg, 3 times / day
Route: oral
Route: multiple
Dose: 450 mg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/15587753/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: FED
Sources:
https://pubmed.ncbi.nlm.nih.gov/15587753/
PubMed

PubMed

TitleDatePubMed
Comparison of the efficacies of oral beta-lactams in selection of Haemophilus influenzae transformants with mutated ftsI genes.
2008-05
Patents

Patents

JP2002541233A
406
US4731361
4

Sample Use Guides

In Vivo Use Guide
Oral antibiotic therapy (CFPN-PI (CEFCAPENE), 300 mg/day) were started, resulting in gradual improvement of the skin lesion to a PPPASI score of 1 and a VAS score of 2.2 after 2 months
Route of Administration: Oral
In Vitro Use Guide
A spontaneous rifampin-resistant H. influenzae Rd clone, designated RdRIF (19), and two BLNAR isolates (MSC06647 and MSC06663) were used in this study. Cefcapene activity was determined by the broth dilution method. Cefcapene shows potent antimicrobial activity with MIC 0.008mg/ml (for RdRIF), 0.25mg/ml (for MSC06647) and 2 mg/ml (for MSC06663).
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:35:31 GMT 2025
Edited
by admin
on Mon Mar 31 18:35:31 GMT 2025
Record UNII
8I8MJ56XFQ
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CEFCAPENE PIVOXIL
WHO-DD  
Common Name English
CEFCAPENE PIVALOYLOXYMETHYL ESTER
MI  
Preferred Name English
Cefcapene pivoxil [WHO-DD]
Common Name English
CEFCAPENE PIVALOYLOXYMETHYL ESTER [MI]
Common Name English
2,2-DIMETHYLPROPANOYLOXYMETHYL (6R,7R)-7-(((Z)-2-(2-AMINO-1,3-THIAZOL-4-YL)PENT-2-ENOYL)AMINO)-3-(CARBAMOYLOXYMETHYL)-8-OXO-5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLATE
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C357
Created by admin on Mon Mar 31 18:35:31 GMT 2025 , Edited by admin on Mon Mar 31 18:35:31 GMT 2025
Code System Code Type Description
SMS_ID
100000084982
Created by admin on Mon Mar 31 18:35:31 GMT 2025 , Edited by admin on Mon Mar 31 18:35:31 GMT 2025
PRIMARY
PUBCHEM
5282438
Created by admin on Mon Mar 31 18:35:31 GMT 2025 , Edited by admin on Mon Mar 31 18:35:31 GMT 2025
PRIMARY
MERCK INDEX
m3190
Created by admin on Mon Mar 31 18:35:31 GMT 2025 , Edited by admin on Mon Mar 31 18:35:31 GMT 2025
PRIMARY Merck Index
DRUG CENTRAL
532
Created by admin on Mon Mar 31 18:35:31 GMT 2025 , Edited by admin on Mon Mar 31 18:35:31 GMT 2025
PRIMARY
WIKIPEDIA
Cefcapene pivoxil
Created by admin on Mon Mar 31 18:35:31 GMT 2025 , Edited by admin on Mon Mar 31 18:35:31 GMT 2025
PRIMARY
FDA UNII
8I8MJ56XFQ
Created by admin on Mon Mar 31 18:35:31 GMT 2025 , Edited by admin on Mon Mar 31 18:35:31 GMT 2025
PRIMARY
EPA CompTox
DTXSID7049134
Created by admin on Mon Mar 31 18:35:31 GMT 2025 , Edited by admin on Mon Mar 31 18:35:31 GMT 2025
PRIMARY
NCI_THESAURUS
C98218
Created by admin on Mon Mar 31 18:35:31 GMT 2025 , Edited by admin on Mon Mar 31 18:35:31 GMT 2025
PRIMARY
EVMPD
SUB01110MIG
Created by admin on Mon Mar 31 18:35:31 GMT 2025 , Edited by admin on Mon Mar 31 18:35:31 GMT 2025
PRIMARY
CAS
105889-45-0
Created by admin on Mon Mar 31 18:35:31 GMT 2025 , Edited by admin on Mon Mar 31 18:35:31 GMT 2025
PRIMARY
Related Record Type Details
Structure of CEFCAPENE PIVOXIL HYDROCHLORIDE
SALT/SOLVATE -> PARENT
Structure of CEFCAPENE PIVOXIL HYDROCHLORIDE MONOHYDRATE
SALT/SOLVATE -> PARENT
Related Record Type Details
Structure of CEFCAPENE
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